JP2018154622A - 有機化合物、発光素子、発光装置、電子機器、および照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP2018154622A JP2018154622A JP2018048117A JP2018048117A JP2018154622A JP 2018154622 A JP2018154622 A JP 2018154622A JP 2018048117 A JP2018048117 A JP 2018048117A JP 2018048117 A JP2018048117 A JP 2018048117A JP 2018154622 A JP2018154622 A JP 2018154622A
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- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 6
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- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 4
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- CMLCVSPDRZVSRT-UHFFFAOYSA-N n,9-diphenyl-n-(9,9'-spirobi[fluorene]-2-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 CMLCVSPDRZVSRT-UHFFFAOYSA-N 0.000 description 1
- BBNZOXKLBAWRSH-UHFFFAOYSA-N n,9-diphenyl-n-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 BBNZOXKLBAWRSH-UHFFFAOYSA-N 0.000 description 1
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- CRWAGLGPZJUQQK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-[2-[4-(n-(4-carbazol-9-ylphenyl)anilino)phenyl]ethenyl]-n-phenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 CRWAGLGPZJUQQK-UHFFFAOYSA-N 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- NYESPUIMUJRIAP-UHFFFAOYSA-N naphtho[1,2-e][1]benzofuran Chemical group C1=CC=CC2=C3C(C=CO4)=C4C=CC3=CC=C21 NYESPUIMUJRIAP-UHFFFAOYSA-N 0.000 description 1
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229960000286 proflavine Drugs 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
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- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001195 ultra high performance liquid chromatography Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
本実施の形態では、本発明の一態様である有機化合物について説明する。
まず、下記一般式(G1)で表される有機化合物の合成方法の一例について説明する。
次に、下記一般式(G3)で表される有機化合物の合成方法の一例について説明する。
本実施の形態では、実施の形態1で示した有機化合物を用いた発光素子について図1を用いて説明する。
まず、発光素子の基本的な構造について説明する。図1(A)には、一対の電極間に発光層を含むEL層を有する発光素子を示す。具体的には、第1の電極101と第2の電極102との間にEL層103が挟まれた構造を有する。
次に、本発明の一態様である発光素子の具体的な構造および作製方法について、図1を用いて説明する。また、ここでは、図1(B)に示すタンデム構造を有し、マイクロキャビティ構造を備えた発光素子についても図1(D)を用いて説明する。図1(D)に示す発光素子がマイクロキャビティ構造を有する場合は、第1の電極101を反射電極として形成し、第2の電極102を半透過・半反射電極として形成する。従って、所望の電極材料を単数または複数用い、単層または積層して形成することができる。なお、第2の電極102は、EL層103bを形成した後、上記と同様に材料を選択して形成する。また、これらの電極の作製には、スパッタ法や真空蒸着法を用いることができる。
第1の電極101および第2の電極102を形成する材料としては、上述した両電極の機能が満たせるのであれば、以下に示す材料を適宜組み合わせて用いることができる。例えば、金属、合金、電気伝導性化合物、およびこれらの混合物などを適宜用いることができる。具体的には、In−Sn酸化物(ITOともいう)、In−Si−Sn酸化物(ITSOともいう)、In−Zn酸化物、In−W−Zn酸化物が挙げられる。その他、アルミニウム(Al)、チタン(Ti)、クロム(Cr)、マンガン(Mn)、鉄(Fe)、コバルト(Co)、ニッケル(Ni)、銅(Cu)、ガリウム(Ga)、亜鉛(Zn)、インジウム(In)、スズ(Sn)、モリブデン(Mo)、タンタル(Ta)、タングステン(W)、パラジウム(Pd)、金(Au)、白金(Pt)、銀(Ag)、イットリウム(Y)、ネオジム(Nd)などの金属、およびこれらを適宜組み合わせて含む合金を用いることもできる。その他、上記例示のない元素周期表の第1族または第2族に属する元素(例えば、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、ストロンチウム(Sr))、ユウロピウム(Eu)、イッテルビウム(Yb)などの希土類金属およびこれらを適宜組み合わせて含む合金、その他グラフェン等を用いることができる。
正孔注入層(111、111a、111b)は、陽極である第1の電極101や電荷発生層(104)からEL層(103、103a、103b)に正孔(ホール)を注入する層であり、正孔注入性の高い材料を含む層である。
発光層(113、113a、113b、113c)は、発光物質を含む層である。なお、発光物質としては、青色、紫色、青紫色、緑色、黄緑色、黄色、橙色、赤色などの発光色を呈する物質を適宜用いる。また、複数の発光層(113a、113b、113c)に異なる発光物質を用いることにより異なる発光色を呈する構成(例えば、補色の関係にある発光色を組み合わせて得られる白色発光)とすることができる。さらに、一つの発光層が異なる発光物質を有する積層構造であっても良い。
電子輸送層(114、114a、114b)は、電子注入層(115、115a、115b)によって、第2の電極102や電荷発生層(104)から注入された電子を発光層(113、113a、113b)に輸送する層である。なお、電子輸送層(114、114a、114b)は、電子輸送性材料を含む層である。電子輸送層(114、114a、114b)に用いる電子輸送性材料は、1×10−6cm2/Vs以上の電子移動度を有する物質が好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、これら以外のものを用いることができる。
電子注入層(115、115a、115b)は、電子注入性の高い物質を含む層である。電子注入層(115、115a、115b)には、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。また、電子注入層(115、115a、115b)にエレクトライドを用いてもよい。エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。なお、上述した電子輸送層(114、114a、114b)を構成する物質を用いることもできる。
電荷発生層104は、第1の電極(陽極)101と第2の電極(陰極)102との間に電圧を印加したときに、EL層103aに電子を注入し、EL層103bに正孔を注入する機能を有する。なお、電荷発生層104は、正孔輸送性材料に電子受容体(アクセプター)が添加された構成であっても、電子輸送性材料に電子供与体(ドナー)が添加された構成であってもよい。また、これらの両方の構成が積層されていても良い。なお、上述した材料を用いて電荷発生層104を形成することにより、EL層が積層された場合における駆動電圧の上昇を抑制することができる。
本実施の形態で示した発光素子は、様々な基板上に形成することができる。なお、基板の種類は、特定のものに限定されることはない。基板の一例としては、半導体基板(例えば単結晶基板又はシリコン基板)、SOI基板、ガラス基板、石英基板、プラスチック基板、金属基板、ステンレス・スチル基板、ステンレス・スチル・ホイルを有する基板、タングステン基板、タングステン・ホイルを有する基板、可撓性基板、貼り合わせフィルム、繊維状の材料を含む紙、又は基材フィルムなどが挙げられる。
本実施の形態では、本発明の一態様である発光装置について説明する。なお、図2(A)に示す発光装置は、第1の基板201上のトランジスタ(FET)202と発光素子(203R、203G、203B、203W)が電気的に接続されてなるアクティブマトリクス型の発光装置であり、複数の発光素子(203R、203G、203B、203W)は、共通のEL層204を有し、また、各発光素子の発光色に応じて、各発光素子の電極間の光学距離が調整されたマイクロキャビティ構造を有する。また、EL層204から得られた発光が第2の基板205に形成されたカラーフィルタ(206R、206G、206B)を介して射出されるトップエミッション型の発光装置である。
本実施の形態では、本発明の一態様である発光装置について説明する。
本実施の形態では、本発明の一態様である発光装置、本発明の一態様である発光素子を有する表示装置を適用して完成させた様々な電子機器や自動車の一例について、説明する。
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光素子を適用して作製される照明装置の構成について図7を用いて説明する。
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光素子を適用して作製される照明装置の応用例について、図8を用いて説明する。
本実施例では、本発明の一態様の有機化合物であり、実施の形態1において構造式(100)で表される、8−[3’−(ジベンゾチオフェン−4−イル)(1,1’−ビフェニル−3−イル)]ナフト[1’,2’:4,5]フロ[3,2−d]ピリミジン(略称:8mDBtBPNfpm)の合成方法について説明する。なお、8mDBtBPNfpmの構造を以下に示す。
まず、2−ヒドロキシナフタレン−1−カルボニトリル4.0g、炭酸カリウム6.6gをフラスコに入れ、フラスコ内を窒素置換し、30mLのDMFと、ブロモ酢酸エチル4.0gを加え、80℃で16時間加熱した。得られた反応物を100mLの氷水に加えて急冷し、1時間撹拌した後ろ過した。得られたろ物を水で洗浄し、エタノールと水で再結晶することにより目的物(茶色固体)4.4gを収率72%で得た。ステップ1の合成スキームを下記式(a−1)に示す。
次に、上記ステップ1で合成した1−アミノ−ナフト[2,1−b]フラン−2−カルボン酸エチル4.4g、ホルムアミジン酢酸塩1.8g、25mLのホルムアミドをフラスコに入れ、160℃で8時間加熱した。得られた反応物に100mLの水を加えてろ過し、ろ物を水で洗浄することにより、目的物(褐色固体)3.9gを収率96%で得た。ステップ2の合成スキームを下記式(a−2)に示す。
次に、上記ステップ2で合成したナフト[1’,2’:4,5]フロ[3,2−d]ピリミジン−8(9H)−オン3.9gと、15mLの塩化ホスホリルをフラスコに入れ、窒素気流下にて100℃で6時間加熱した。得られた反応物を100mLの氷水に加えて急冷した後、3Mの水酸化ナトリウム水溶液330mLを加え、1時間撹拌した。これをろ過し、ろ物をエタノールで洗浄し、目的物(黄色固体)1.8gを42%の収率で得た。ステップ3の合成スキームを下記式(a−3)に示す。
次に、上記ステップ3で合成した8−クロロ−ナフト[1’,2’:4,5]フロ[3,2−d]ピリミジン1.8g、3−(ジベンゾチオフェン−4−イル)フェニルボロン酸2.9g、15mLの2Mの炭酸カリウム水溶液、150mLのトルエン、および15mLのエタノールを加え、フラスコ内を窒素置換した。この混合物にテトラキス(トリフェニルホスフィン)パラジウム(0)0.29gを加え、窒素気流下にて95℃で12時間加熱した。得られた反応物をろ過し、得られたろ物を水、エタノールを用いて順次洗浄した。
本実施例では、実施の形態1の構造式(101)で表される本発明の一態様である有機化合物、10−[3’−(ジベンゾチオフェン−4−イル)(1,1’−ビフェニル−3−イル)]ナフト[2’,1’:4,5]フロ[3,2−d]ピリミジン(略称:10mDBtBPNfpm(II))の合成方法について説明する。なお、10mDBtBPNfpm(II)の構造を以下に示す。
まず、1−ヒドロキシナフタレン−2−カルボニトリル4.9g、炭酸カリウム8.1gをフラスコに入れ、フラスコ内を窒素置換し、40mLのDMFと、ブロモ酢酸エチル4.9gを加え、80℃で15時間加熱した。得られた反応物を100mLの氷水に加えて急冷し、2時間撹拌した後ろ過した。得られたろ物を水で洗浄し、エタノールと水で再結晶することにより目的物(灰色固体)5.2gを収率70%で得た。ステップ1の合成スキームを下記式(b−1)に示す。
次に、上記ステップ1で合成した3−アミノ−ナフト[1,2−b]フラン−2−カルボン酸エチル5.2g、ホルムアミジン酢酸塩4.2g、28mLのホルムアミドをフラスコに入れ、160℃で5時間加熱した。得られた反応物に100mLの水を加えてろ過し、ろ物を水で洗浄することにより、目的物(茶色固体)4.8gを収率95%で得た。ステップ2の合成スキームを下記式(b−2)に示す。
次に、上記ステップ2で合成したナフト[2’,1’:4,5]フロ[3,2−d]ピリミジン−10(9H)−オン4.6gと、18mLの塩化ホスホリルをフラスコに入れ、窒素気流下にて100℃で7時間加熱した。得られた反応物を100mLの氷水に加えて急冷した後、3Mの水酸化ナトリウム水溶液400mLを加え、1時間撹拌した。これをろ過し、ろ物をエタノールで洗浄し、目的物(茶色固体)3.9gを78%の収率で得た。ステップ3の合成スキームを下記式(b−3)に示す。
次に、上記ステップ3で合成した10−クロロ−ナフト[2’,1’:4,5]フロ[3,2−d]ピリミジン1.8g、3−(ジベンゾチオフェン−4−イル)フェニルボロン酸1.2g、15mLの2Mの炭酸カリウム水溶液、150mLのトルエン、および15mLのエタノールをフラスコに加え、フラスコ内を窒素置換した。この混合物に0.49gのビス(トリフェニルホスフィン)パラジウム(II)ジクロリドを加え、窒素気流下にて95℃で加熱した。得られた反応物をろ過し、得られたろ物を水、エタノールを用いて順次洗浄した。
本実施例で示す発光素子は、図13に示すように基板900上に形成された第1の電極901上に正孔注入層911、正孔輸送層912、発光層913、電子輸送層914、電子注入層915が順次積層され、電子注入層915上に第2の電極903が積層された構造を有する。
作製した各発光素子の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
作製した発光素子4および発光素子5の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
作製した発光素子6および比較発光素子7の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
本実施例では、実施の形態1の構造式(103)で表される本発明の一態様である有機化合物、10−[3’−(ジベンゾチオフェン−4−イル)ビフェニル−3−イル]フェナントロ[9’,10’:4,5]フロ[3,2−d]ピリミジン(略称:10mDBtBPPnfpm)の合成方法について説明する。なお、10mDBtBPPnfpmの構造を以下に示す。
102 第2の電極
103 EL層
103a、103b、103c EL層
104 電荷発生層
111、111a、111b 正孔注入層
112、112a、112b 正孔輸送層
113、113a、113b、113c 発光層
114、114a、114b 電子輸送層
115、115a、115b 電子注入層
201 第1の基板
202 トランジスタ(FET)
203R、203G、203B、203W 発光素子
204 EL層
205 第2の基板
206R、206G、206B カラーフィルタ
206R’、206G’、206B’ カラーフィルタ
207 第1の電極
208 第2の電極
209 黒色層(ブラックマトリックス)
210R、210G 導電層
301 第1の基板
302 画素部
303 駆動回路部(ソース線駆動回路)
304a、304b 駆動回路部(ゲート線駆動回路)
305 シール材
306 第2の基板
307 引き回し配線
308 FPC
309 FET
310 FET
311 FET
312 FET
313 第1の電極
314 絶縁物
315 EL層
316 第2の電極
317 発光素子
318 空間
900 基板
901 第1の電極
902 EL層
903 第2の電極
911 正孔注入層
912 正孔輸送層
913 発光層
914 電子輸送層
915 電子注入層
4000 照明装置
4001 基板
4002 発光素子
4003 基板
4004 第1の電極
4005 EL層
4006 第2の電極
4007 電極
4008 電極
4009 補助配線
4010 絶縁層
4011 封止基板
4012 シール材
4013 乾燥剤
4015 拡散板
4100 照明装置
4200 照明装置
4201 基板
4202 発光素子
4204 第1の電極
4205 EL層
4206 第2の電極
4207 電極
4208 電極
4209 補助配線
4210 絶縁層
4211 封止基板
4212 シール材
4213 バリア膜
4214 平坦化膜
4215 拡散板
4300 照明装置
5101 ライト
5102 ホイール
5103 ドア
5104 表示部
5105 ハンドル
5106 シフトレバー
5107 座席シート
5108 インナーリアビューミラー
7000 筐体
7001 表示部
7002 第2表示部
7003 スピーカ
7004 LEDランプ
7005 操作キー
7006 接続端子
7007 センサ
7008 マイクロフォン
7009 スイッチ
7010 赤外線ポート
7011 記録媒体読込部
7012 支持部
7013 イヤホン
7014 アンテナ
7015 シャッターボタン
7016 受像部
7018 スタンド
7019 マイクロフォン
7020 カメラ
7021 外部接続部
7022、7023 操作用ボタン
7024 接続端子
7025 バンド
7026 留め金
7027 時刻を表すアイコン
7028 その他のアイコン
8001 照明装置
8002 照明装置
8003 照明装置
8004 照明装置
9310 携帯情報端末
9311 表示部
9312 表示領域
9313 ヒンジ
9315 筐体
Claims (16)
- 一般式(G1)で表される有機化合物。
(式中、Aは炭素数6乃至100の基であり、芳香環または複素芳香環を少なくとも含む。なお、前記芳香環および前記複素芳香環は置換基を有していても良い。また、Qは酸素または硫黄を表す。また、環Xは、置換もしくは無置換のナフタレン環、または置換もしくは無置換のフェナントレン環を表す。) - 請求項1において、
前記Aは、ベンゼン環、ナフタレン環、フルオレン環、フェナントレン環、トリフェニレン環、ジベンゾチオフェン環を含む複素芳香環、ジベンゾフラン環を含む複素芳香環、カルバゾール環を含む複素芳香環、ベンゾイミダゾール環、トリフェニルアミン構造のいずれか一または複数で構成され、前記環または前記構造は、置換基を有していてもよい。 - 一般式(G2)で表される有機化合物。
(式中、αは置換もしくは無置換のフェニレン基を表し、nは0乃至4の整数を表す。また、Htuniは正孔輸送性を有する骨格を表す。また、Qは酸素または硫黄を表す。また、環Xは、置換もしくは無置換のナフタレン環、または置換もしくは無置換のフェナントレン環を表す。) - 一般式(G3)で表される有機化合物。
(式中、αは置換もしくは無置換のフェニレン基を表し、nは1乃至4の整数を表す。また、Htuniは正孔輸送性を有する骨格を表す。また、R1は、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数5乃至7の単環式飽和炭化水素、置換もしくは無置換の炭素数7乃至10の多環式飽和炭化水素、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Qは酸素または硫黄を表す。また、環Xは置換もしくは無置換のナフタレン環、置換もしくは無置換のフェナントレン環を表す。) - 一般式(G4)で表される有機化合物。
(式中、Htuniは正孔輸送性を有する骨格を表す。また、R1は、水素、炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数5乃至7の単環式飽和炭化水素、置換もしくは無置換の炭素数7乃至10の多環式飽和炭化水素、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Qは酸素または硫黄を表す。また、環Xは置換もしくは無置換のナフタレン環、置換もしくは無置換のフェナントレン環を表す。) - 一般式(G5)で表される有機化合物。
(式中、Htuniは正孔輸送性を有する骨格を表す。また、Qは酸素または硫黄を表す。また、環Xは置換もしくは無置換のナフタレン環、置換もしくは無置換のフェナントレン環を表す。) - 請求項3乃至請求項6のいずれか一において、
前記Htuniは、ピロール環構造、フラン環構造、チオフェン環構造を有する有機化合物。 - 請求項3乃至請求項7のいずれか一において、
前記Htuniは、下記一般式(Ht−1)〜(Ht−7)のいずれかで表される有機化合物。
(式中、R2〜R15はそれぞれ1乃至4の置換基を表し、かつそれぞれ独立に水素、炭素数1〜6のアルキル基、置換もしくは無置換のフェニル基のいずれかを表す。また、Ar1は、置換もしくは無置換の炭素数6乃至13のアリール基を表す。) - 請求項1乃至請求項6のいずれか一において、
前記環Xは、下記一般式(X−1)〜(X−4)のいずれかで表され、かつaで表される位置で隣接する環と縮合する有機化合物。
(式中、R16、R18、およびR20はそれぞれ1または2の置換基を表し、R17、R19、およびR21〜R23はそれぞれ1乃至4の置換基を表し、かつR16〜R23は、それぞれ独立に水素、炭素数1〜6のアルキル基、置換もしくは無置換のフェニル基のいずれかを表す。) - 構造式(100)または構造式(101)で表される有機化合物。
- 請求項1乃至請求項10のいずれか一に記載の有機化合物を用いた発光素子。
- 一対の電極間にEL層を有し、
前記EL層は、請求項1乃至請求項10のいずれか一に記載の有機化合物を有する発光素子。 - 一対の電極間にEL層を有し、
前記EL層は、発光層を有し、
前記発光層は、請求項1乃至請求項10のいずれか一に記載の有機化合物を有する発光素子。 - 請求項11乃至請求項13のいずれか一に記載の発光素子と、
トランジスタ、または基板の少なくとも一と、
を有する発光装置。 - 請求項14に記載の発光装置と、
マイク、カメラ、操作用ボタン、外部接続部、または、スピーカの少なくとも一と、
を有する電子機器。 - 請求項11乃至請求項13のいずれか一に記載の発光素子と、
筐体、カバー、または、支持台の少なくとも一と、
を有する照明装置。
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